Thionyl Chloride → HCID 18509223, compound

HRID 1356695Notes

Reaction equation

HRID 1356695 reaction equation
[Cl:1][C:2]1[CH:10]=[C:6]([C:7](O)=[O:8])[C:5]([N:11]([CH3:22])[S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:4][CH:3]=1.S(Cl)(Cl)=O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:11]([CH3:22])[S:12]([C:15]2[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=2)(=[O:13])=[O:14])=[C:6]([CH2:7][OH:8])[CH:10]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 18509230HCID 18509230, compound

Product 1

HCID 18509223HCID 18509223, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5-chloro-N-methyl-N-(p-toluenesulfonyl)anthranilic acid (5.20 g (15.3 mmol)) in chloroform (20.0 ml), thionyl chloride (2.00 g (27.4 mmol)) was added with stirring at room temperature. The resulting mixture was heated at 50° C. for 2 hours with stirring and then concentrated under reduced pressure. The residue was dissolved in acetonitrile (20.0 ml) and added dropwise to a solution of sodium borohydride (90%, 1.30 g (30.9 mmol) in water (20.0 ml) under cooling with ice. After one hour's stirring at room temperature, water (100.0 ml) was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The extract was washed with dilute hydrochloric acid, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 4.40 g (88%) of the title compound as white crystals.

Workup

  1. temperatureThe resulting mixture was heated at 50° C. for 2 hours
  2. stirringwith stirring
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in acetonitrile (20.0 ml)
  5. additionadded dropwise to a solution of sodium borohydride (90%, 1.30 g (30.9 mmol) in water (20.0 ml)
  6. temperatureunder cooling with ice
  7. stirringAfter one hour's stirring at room temperature
  8. additionwater (100.0 ml) was added to the reaction mixture
  9. extractionthe resulting mixture was extracted with ethyl acetate
  10. washThe extract was washed with dilute hydrochloric acid
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-74f5124c9d9b4a7bb5323c0e70c15c4b
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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